Bis(adenosine)-5'-pentaphosphate

Details

• Internal ID: 77788119-c8e9-4926-a145-8114ffdfc561
• Taxonomy: Nucleosides, nucleotides, and analogues > (5->5)-dinucleotides
• IUPAC Name: bis[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate
• SMILES (Canonical): C1=NC(=C2C(=N1)N(C=N2)C3C(C(C(O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OCC4C(C(C(O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)N
• SMILES (Isomeric): C1=NC(=C2C(=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)COP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OP(=O)(O)OC[C@@H]4[C@H]([C@H]([C@@H](O4)N5C=NC6=C(N=CN=C65)N)O)O)O)O)N
• InChI: InChI=1S/C20H29N10O22P5/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)30-6-28-10-16(22)24-4-26-18(10)30/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H,43,44)(H2,21,23,25)(H2,22,24,26)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1
• InChI Key: OIMACDRJUANHTJ-XPWFQUROSA-N
• Popularity: 251 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₉N₁₀O₂₂P₅
• Molecular Weight: 916.40 g/mol
• Exact Mass: 916.01459758 g/mol
• Topological Polar Surface Area (TPSA): 481.00 Ų
• XlogP: -9.40
• Atomic LogP (AlogP): -2.33
• H-Bond Acceptor: 27
• H-Bond Donor: 11
• Rotatable Bonds: 16

Synonyms

• RefChem:568980
• 41708-91-2
• ApppppA
• Diadenosine Pentaphosphate
• Ap5ACN
• EINECS 255-507-1
• di(adenosine-5')pentaphosphate
• P1,P5-Bis-(5'-adenosyl)pentaphosphate
• CHEMBL437508
• Adenosine-(5')-pentaphospho-(5')-adenosine
• P(1),P(5)-bis(5'-adenosyl) pentaphosphate
• Adenosine 5'-(hexahydrogen pentaphosphate), 5'.5'-ester with adenosine
• P1,P5-di(adenosine-5')pentaphosphate
• adenosine(5')pentaphospho(5')adenosine
• Bis(5'-adenosyl) pentaphosphate
• bis[[[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate
• Adenosine 5'-(hexahydrogen pentaphosphate), P''''-->5'-ester with adenosine
• P1,P5-Bis(5'-adenosyl) pentaphosphate
• 2bzz
• orb64071
• 14220-10-1
• orb1733903
• orb3135720
• SCHEMBL2934890
• SCHEMBL30583138
• CHEBI:28898
• DTXSID501379827
• BDBM50435017
• EX-A14867
• DB01717
• P1,P5-Bis(5'-adenosyl)pentaphosphate
• NS00073119
• C04058
• T211332
• Q27103950
• Adenosine 5a(2)-pentaphosphate, 5a(2)-5a(2)-ester with adenosine

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6304	63.04%
Caco-2	-	0.8573	85.73%
Blood Brain Barrier	+	0.6000	60.00%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.3275	32.75%
OATP2B1 inhibitior	-	0.7142	71.42%
OATP1B1 inhibitior	+	0.9548	95.48%
OATP1B3 inhibitior	+	0.9470	94.70%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.7760	77.60%
P-glycoprotein inhibitior	+	0.7407	74.07%
P-glycoprotein substrate	-	0.8138	81.38%
CYP3A4 substrate	+	0.5081	50.81%
CYP2C9 substrate	-	0.8110	81.10%
CYP2D6 substrate	-	0.8643	86.43%
CYP3A4 inhibition	-	0.7715	77.15%
CYP2C9 inhibition	-	0.9107	91.07%
CYP2C19 inhibition	-	0.9003	90.03%
CYP2D6 inhibition	-	0.9012	90.12%
CYP1A2 inhibition	-	0.8771	87.71%
CYP2C8 inhibition	-	0.7553	75.53%
CYP inhibitory promiscuity	-	0.8910	89.10%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.5334	53.34%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.8982	89.82%
Skin irritation	-	0.7641	76.41%
Skin corrosion	-	0.9266	92.66%
Ames mutagenesis	-	0.8100	81.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7574	75.74%
Micronuclear	+	1.0000	100.00%
Hepatotoxicity	-	0.5986	59.86%
skin sensitisation	-	0.8491	84.91%
Respiratory toxicity	+	0.9556	95.56%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.7359	73.59%
Acute Oral Toxicity (c)	III	0.4581	45.81%
Estrogen receptor binding	+	0.7633	76.33%
Androgen receptor binding	+	0.7932	79.32%
Thyroid receptor binding	+	0.6134	61.34%
Glucocorticoid receptor binding	+	0.6758	67.58%
Aromatase binding	+	0.6613	66.13%
PPAR gamma	+	0.7190	71.90%
Honey bee toxicity	-	0.7491	74.91%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.4880	48.80%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4315	P47900	Purinergic receptor P2Y1	426 nM; 760 nM	EC50; EC50	via Super-PRED; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.38%	96.09%
CHEMBL1075162	Q13304	Uracil nucleotide/cysteinyl leukotriene receptor	98.14%	80.33%
CHEMBL3137261	O14744	PRMT5/MEP50 complex	94.33%	100.00%
CHEMBL4040	P28482	MAP kinase ERK2	93.98%	83.82%
CHEMBL2243	O00519	Anandamide amidohydrolase	91.30%	97.53%
CHEMBL3401	O75469	Pregnane X receptor	91.28%	94.73%
CHEMBL226	P30542	Adenosine A1 receptor	86.64%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.76%	95.89%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.99%	94.00%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	83.80%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.51%	89.00%
CHEMBL4523377	Q86WV6	Stimulator of interferon genes protein	83.05%	95.48%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.91%	86.33%
CHEMBL3891	P07384	Calpain 1	82.28%	93.04%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	82.16%	99.23%
CHEMBL5524	Q99873	Protein-arginine N-methyltransferase 1	82.03%	96.67%
CHEMBL5957	P21589	5'-nucleotidase	81.54%	97.78%
CHEMBL221	P23219	Cyclooxygenase-1	81.28%	90.17%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.83%	99.17%
CHEMBL3137262	O60341	LSD1/CoREST complex	80.01%	97.09%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 440210
• LOTUS: LTS0213592
• wikiData: Q27103950